1. Field of the Invention
This invention relates to new and useful nonsteroidal anti-inflammatory agents. More particularly, it relates to certain N-(substituted)-1-heteroaryloxindole-3-carboxamides which are potent inhibitors of cyclooxygenase (CO) and lipoxygenase (LO) and which are of value as anti-inflammatory agents in mammals.
2. Description of Related Art
U.S. Pat. No. 3,634,453, issued Jan. 11, 1972, describes a series of anti-inflammatory N-(substituted)oxindole-3-carboxamides, the 1-position of which may be substituted by, inter alia, C.sub.1-6 alkyl or phenylalkyl; and the carboxamide moiety of which carries a phenyl, substituted phenyl or naphthyl group.
Oxindole-3-(N-2-thiazolyl)carboxamides, the 1-position of which is unsubstituted or bears an alkyl, aryl or aralkyl group, and their use as antipyretic, analgesic and anti-inflammatory agents are disclosed in U.S. Pat. No. 3,749,731, issued July 31, 1973. Each of U.S. Pat. No. 4,644,005 and 4,686,224 describes N-(substituted)-1-phenyl oxindole-3-carboxamides wherein a monoor bicyclic ring system is fused to the 5,6-positions of the oxindole and wherein the N-substituent can be pyridyl or 2-thiazolyl. The compounds are anti-inflammatory agents.
Tricyclic oxindole 3-carboxamides, the 1-position of which is substituted with a phenyl group, and the carboxamide moiety of which bears a phenyl, substituted phenyl or heterocyclyl moiety, and their use as anti-inflammatory agents are disclosed in U.S. Pat. No. 4,695,571.
U.S. Pat. No. 4,730,004 discloses anti-inflammatory 1-acyloxindole-3-carboxamides, the carboxamide moiety of which is substituted by a heterocyclic (thienyl, furyl, thiazolyl, etc.), furylmethyl, thenyl or substituted phenyl group.
A variety of anti-inflammatory oxindoles, the 1,3-positions of which are substituted by carboxamide or substituted carboxamide groups; or the 1-position of which bears a carboxamide group and the 3-position an acyl group, or vice versa, are known. However, said oxindoles are structurally different from the oxindoles of this invention and are merely mentioned to indicate the rather extensive and intensive efforts to develop non-steroidal anti-inflammatory agents.